(Diethylamino)sulfur trifluoride → HCID 18782508, compound

HRID 1420820Notes

Reaction equation

HRID 1420820 reaction equation
O[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=1[Br:16].C(N(S(F)(F)[F:23])CC)C>ClCCl>[F:23][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=1[Br:16]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 18782554HCID 18782554, compound

Product 1

HCID 18782508HCID 18782508, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (-78° C.) suspension of 2-(2-hydroxyethoxy)-5-(trifluoromethoxy)bromobenzene (Description 30; 8.9 g, 30 mmol). in dichoromethane (80 ml) was added diethylaminosulphur trifluoride (3.88 ml, 31.5 mmol). The solution was stirred at ambient temperature for 2 h., then quenched by the dropwise addition of water (100 ml). The organic layer was separated, washed with brine (100 ml), dried (MgSO4), and evaporated in vacuo. Purification in silica, eluting with 15%-20% ethyl acetate in hexane gave the title compound as a clear oil (1.9 g, 15%). 1H NMR (360 MHz, CDCl3) δ4.23 (1H, m), 4.31 (1H, m), 4.37 (1H, m), 4.86 (1H, m), 6.90 (1H, m), 7.15 (1H, m), and 7.47 (1H, t, J 0.7 Hz).

Workup

  1. temperatureTo a cooled
  2. customquenched by the dropwise addition of water (100 ml)
  3. customThe organic layer was separated
  4. washwashed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customPurification in silica
  8. washeluting with 15%-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ea6d35d662dd45d0b8ad5405edc32ead
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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